Watch rare footage of Diddy and Mase on the Rosie O’Donnell Show
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Watch rare footage of Diddy and Mase on the Rosie O'Donnell Show

Diddy is an iconic figure within hip-hop who has conquered every corner of the record industry. Most known for being the business-savvy executive who discovered Biggie Smalls, the Harlem native has had quite the career. From music to film and television, the mogul has seemingly succeeded at everything he has put his mind to and is still a formidable force within hip-hop. Born Sean Combs in uptown Manhattan, the businessman formerly known as Puff Daddy has been responsible for several artists, including the one and only Mase.

As an adolescent living between Harlem and the suburban neighbourhood of Mount Vernon, Combs found himself racing around New York in the late 1980s, and as an inquisitive African-American, he found himself getting involved in the New York hip-hop scene. At 19, while socialising with industry heads in Harlem, Combs became close with Andre Harrell, the then-president of Uptown Records, who hired a keen Diddy. Here he learned the music business, from producing to A&Ring.

Diddy, whose father was murdered in uptown Manhattan, knew Harlem well and was a highly-connected and respected figure. However, while he rapidly rose up the ranks of Uptown Records, new young talent surfaced, and one Harlem-based crew was beginning to turn heads. Headed by Big L, during the early ’90s, Children of the Corn was the pride and joy of Harlem. Comprised of Big L, Cam’Ron, Mase (real name Mason Betha), Herb McGruff, and Bloodshed, the collective was short-lived yet made a lot of noise.

In 1993, Diddy was fired by Harrell. But with a knack for producing and scouting talent, after working there for several years, aged 24, he founded Bad Boy Entertainment in 1993. Looking for a solo career, in 1996, Mase’s sister Stason introduced him to her friend Cudda Love, the road manager for Biggie Smalls. Love then took the young prodigy child to meet Combs, who signed him on the spot. Mase and Diddy quickly became close and developed a brotherly relationship.

As such, in 1997, Diddy (then known as Puff Daddy) took Betha with him on the Rosie O’Donnell Show, a popular daytime talk show. You can watch the rare footage of the show in the video below.